| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,408.55 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,295.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,689.86 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $2,920.47 | Reimagined |
| 2020 | $3,840.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $5,160.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $3,400.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $3,600.00 | Wellesley to Bourne (1-Day, Sat) |
